CH383972A - Procédé de préparation de phényloxyméthyl-2-oxazolidinones - Google Patents
Procédé de préparation de phényloxyméthyl-2-oxazolidinonesInfo
- Publication number
- CH383972A CH383972A CH6582558A CH6582558A CH383972A CH 383972 A CH383972 A CH 383972A CH 6582558 A CH6582558 A CH 6582558A CH 6582558 A CH6582558 A CH 6582558A CH 383972 A CH383972 A CH 383972A
- Authority
- CH
- Switzerland
- Prior art keywords
- oxazolidinone
- atoms
- groupe
- représente
- renfermant
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 6
- VHNHOAFXJMMMHV-UHFFFAOYSA-N 3-(phenoxymethyl)-1,3-oxazolidin-2-one Chemical class O=C1OCCN1COC1=CC=CC=C1 VHNHOAFXJMMMHV-UHFFFAOYSA-N 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 241000404305 Erica arborea Species 0.000 claims 2
- 239000003610 charcoal Substances 0.000 claims 2
- 239000003245 coal Substances 0.000 claims 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 16
- 239000000203 mixture Substances 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 14
- -1 5-(m-methoxyphenoxymethyl)-2-oxazolidinone Chemical compound 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- ZMNSRFNUONFLSP-UHFFFAOYSA-N mephenoxalone Chemical compound COC1=CC=CC=C1OCC1OC(=O)NC1 ZMNSRFNUONFLSP-UHFFFAOYSA-N 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- RJNVSQLNEALZLC-UHFFFAOYSA-N 2-[(2-methoxyphenoxy)methyl]oxirane Chemical compound COC1=CC=CC=C1OCC1OC1 RJNVSQLNEALZLC-UHFFFAOYSA-N 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 238000011065 in-situ storage Methods 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- DSNYFFJTZPIKFZ-UHFFFAOYSA-N propoxybenzene Chemical class CCCOC1=CC=CC=C1 DSNYFFJTZPIKFZ-UHFFFAOYSA-N 0.000 description 4
- ZCZDDIPGOAMPEJ-UHFFFAOYSA-N C(C)N1C(OC(C1)COC1=C(C=CC=C1)OC)=O Chemical compound C(C)N1C(OC(C1)COC1=C(C=CC=C1)OC)=O ZCZDDIPGOAMPEJ-UHFFFAOYSA-N 0.000 description 3
- YUXKQZYGXFJHOA-UHFFFAOYSA-N COC1=C(OCC2CN(C(O2)=O)C)C=CC=C1 Chemical compound COC1=C(OCC2CN(C(O2)=O)C)C=CC=C1 YUXKQZYGXFJHOA-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- BUURBCAOIUVUIY-UHFFFAOYSA-N 1-amino-3-(2-methoxyphenoxy)propan-2-ol Chemical compound COC1=CC=CC=C1OCC(O)CN BUURBCAOIUVUIY-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000003884 phenylalkyl group Chemical group 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003204 tranquilizing agent Substances 0.000 description 2
- 230000002936 tranquilizing effect Effects 0.000 description 2
- GABYGHFEJZTGIU-UHFFFAOYSA-N 1-(2-methoxyphenoxy)-3-(methylamino)propan-2-ol Chemical compound CNCC(O)COC1=CC=CC=C1OC GABYGHFEJZTGIU-UHFFFAOYSA-N 0.000 description 1
- PVUJKBGSDBRWPK-UHFFFAOYSA-N 1-[3-(2-chlorophenoxy)-2-hydroxypropyl]-1-methylurea Chemical compound ClC1=C(OCC(CN(C(=O)N)C)O)C=CC=C1 PVUJKBGSDBRWPK-UHFFFAOYSA-N 0.000 description 1
- WKHJYZWHRAIGPQ-UHFFFAOYSA-N 1-chloro-3-(2-chlorophenoxy)propan-2-ol Chemical compound ClCC(O)COC1=CC=CC=C1Cl WKHJYZWHRAIGPQ-UHFFFAOYSA-N 0.000 description 1
- DJOGZXNBSUIGKG-UHFFFAOYSA-N 2-[(2-ethoxyphenoxy)methyl]oxirane Chemical compound CCOC1=CC=CC=C1OCC1OC1 DJOGZXNBSUIGKG-UHFFFAOYSA-N 0.000 description 1
- AVWGFHZLPMLKBL-UHFFFAOYSA-N 2-[(4-methoxyphenoxy)methyl]oxirane Chemical compound C1=CC(OC)=CC=C1OCC1OC1 AVWGFHZLPMLKBL-UHFFFAOYSA-N 0.000 description 1
- FKPQKHAGDASLEY-UHFFFAOYSA-N 5-[(2-chlorophenoxy)methyl]-1,3-oxazolidin-2-one Chemical compound ClC1=CC=CC=C1OCC1OC(=O)NC1 FKPQKHAGDASLEY-UHFFFAOYSA-N 0.000 description 1
- HKRZKXPHRPQKES-UHFFFAOYSA-N 5-[(3-chlorophenoxy)methyl]-1,3-oxazolidin-2-one Chemical compound ClC1=CC=CC(OCC2OC(=O)NC2)=C1 HKRZKXPHRPQKES-UHFFFAOYSA-N 0.000 description 1
- QYZDEEHEJPYXDQ-UHFFFAOYSA-N 5-[(4-methoxyphenoxy)methyl]-1,3-oxazolidin-2-one Chemical compound C1=CC(OC)=CC=C1OCC1OC(=O)NC1 QYZDEEHEJPYXDQ-UHFFFAOYSA-N 0.000 description 1
- HSRJKNPTNIJEKV-UHFFFAOYSA-N Guaifenesin Chemical compound COC1=CC=CC=C1OCC(O)CO HSRJKNPTNIJEKV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- LEMRINBNPNVYRN-UHFFFAOYSA-N [1-chloro-3-(2-methoxyphenoxy)propan-2-yl] carbamate Chemical compound ClCC(COC1=C(C=CC=C1)OC)OC(N)=O LEMRINBNPNVYRN-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- SURZCVYFPAXNGN-UHFFFAOYSA-N methyl-carbamic acid ethyl ester Chemical compound CCOC(=O)NC SURZCVYFPAXNGN-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Claims (1)
- REVENDICATION Procédé de préparation de phényloxyméthyl-2- oxazolidinone de formule généraledans laquelle le groupe phényle peut être substitué par des radicaux alkoxy ou alcoyle renfermant jus qu'à 6 atomes de carbone ou par des radicaux halo gène, R représentant de l'hydrogène ou un groupe alcoyle ou cycloalcoyle ne renfermant pas plus de 6 atomes de carbone ou un groupe phénylalcoyle ne renfermant pas plus de 10 atomes de carbone, caractérisé en ce qu'on cyclise par chauffage un dérivé phényloxypropane de formule généraledans laquelle le groupe phényl peut être substitué par des groupes alkoxy ou alcoyle renfermant jusqu'à 6 atomes de carbone ou par des groupes halogène dans laquelle Z représente un groupe OH, halogèneU II ou -O-C-NHR, O O II II Y représente -NR-COR', -NR-C-Hal, -NCO O II ou -NR-C-NH@, lorsque Z est un groupe OH, O O <B><U>il il</U></B> Y représente -NR-C-OR' ou NR-COM, lorsque Z est un halogène, et O II Y représente un halogène lorsque Z est -OC-NHR alors que R a la susdite définition, R' représente un résidu alcool et M un métal, et qu'on récupère l'oxazolidinone résultante. SOUS-REVENDICATION Procédé suivant la revendication, caractérisé en ce qu'on alcoyle l'oxazolidinone résultante, si R est de l'hydrogène, pour remplacer l'hydrogène par un groupe alcoyle ou un groupe cycloalcoyle ne renfer mant pas plus de 6 atomes de carbone ou un groupe phénylalcoyle ne renfermant pas plus de 10 atomes de carbone.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69409557A | 1957-11-04 | 1957-11-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH383972A true CH383972A (fr) | 1964-11-15 |
Family
ID=24787380
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH6582558A CH383972A (fr) | 1957-11-04 | 1958-11-04 | Procédé de préparation de phényloxyméthyl-2-oxazolidinones |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH383972A (it) |
-
1958
- 1958-11-04 CH CH6582558A patent/CH383972A/fr unknown
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